This invention relates to novel N-[(1,3,5-triazin-2-yl)aminocarbonyl]arylsulfonamides useful as agricultural chemicals.
Netherlands Patent No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR1## WHEREIN R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Z is methyl or methoxy; or their agriculturally suitable salts; provided that: PA1 (1) those compounds of Formula I, defined above, wherein R.sub.1 is ##STR5## (2) compounds of preference (1) wherein R.sub.3 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, CH.sub.3 S-- or CH.sub.3 CH.sub.2 S--; and PA1 provided that: PA1 (3) compounds of preference (2) wherein X is methyl or alkoxy of 1-3 carbon atoms; and Z is methoxy; PA1 (4) compounds of preference (3) wherein PA1 (5) compounds of preference (3) wherein PA1 (6) compounds of preference (3) wherein PA1 provided that: PA1 (7) compounds of preference (3) wherein PA1 (8) compounds of preference (3) wherein PA1 (9) compounds of preference (8) wherein PA1 (10) compounds of preference (8) wherein PA1 (11) compounds of preference (4) wherein R.sub.3 is nitro and each of R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is hydrogen. PA1 (A) those compounds of Formula I, defined above, wherein ##STR6## (B) compounds of preference (A) wherein Q is sulfur; PA1 (C) Compounds of preference (A) wherein PA1 (1) R.sub.1 is ##STR8## and W is oxygen. PA1 (1) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesu lfonamide, m.p. 174.degree.-178.degree. C.; PA1 (2) n-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfona mide, m.p. 188.degree.-189.degree. C.; and PA1 (3) N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,5-dimethoxybenzenesu lfonamide, m.p. 187.degree.-188.degree. C. PA1 (1) N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 183.degree.-185.degree. C.; PA1 (1) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesu lfonamide, m.p. 174.degree.-178.degree. C.; PA1 (2) n-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 183.degree.-185.degree. C.; and PA1 (3) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chloro-5-methox ybenzenesulfonamide, m.p. 175.degree.-176.degree. C.; PA1 (1) N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 183.degree.-185.degree. C.; PA1 (2) n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide ; PA1 (3) N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 200.degree.-201.degree. C.; and PA1 (4) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesu lfonamide, m.p. 174.degree.-178.degree. C.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug Res. 6, 123 (1974) ##STR2## WHEREIN R is pyridyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops. Some weeds (nutsedge is a particular example) are very difficult to control; many of the herbicides that are used to control nutsedge are so nonselective that they cause damage to the crops themselves.